About this Activity

Spanning nearly five miles through underground corridors, building concourses, food courts, train stations, and sky-bridges, Chicago’s Pedway is the city’s secret weapon against harsh winters. In this case, it also serves as an urban safari. Traveling through these corridors, you’ll learn the history behind the pedway system, covering the unique terrain without the worry of the outdoors. On the way, visit unique locales like City Hall, Chicago Cultural Center, and Macy’s. Listen to the entertaining stories about Chicago’s explosive past and its interesting characters. The coolest part is you’ll be doing all of this underground!

Key Highlights

Price

$25.00 per guest

Duration / Session

2.5 hours

# Sessions

1

Rating

24 positive reviews

Cancellation Policy

Cancellation notice must be provided at least 24 hours prior to the start of the tour.

Reviews

(out of 25 votes)

roadrunner42 .

October 14, 2013

We went on Chicago's Finest Tours, The Roaring Twenties and it was a blast! Dan is a true Irish story teller and keeps his audience enthralled and engaged. You feel like you are on Jeopardy with the various trivia questions he throws out and you learn a great deal along the way. We saw some lovely architecture, found out some factoids about current happenings as well as lots and lots about the 20's. The pace is just right, some walking, some sitting, and the time flies by. Highly recommended. This is the second tour we've taken with Dan and we are looking forward to taking more. A real treat!

CJW W.

October 9, 2013

We had a picture perfect day! We took our parents to Chicago via the train to spend the day. We had booked this tour on-line (cheaper if you book this way) and didn't know what to expect. We were blown away by how much we enjoyed Dan O'Connell and his portrayal of the people and places in Chicago during this timeframe. He used trivia to get everyone involved which was nice, making it interactive. We all said we will remember so much more of the information (because there was a lot of it!!) by the way he shared it! I was worried about the pace of the tour as my mother-in-law walks a bit slower but Dan made us feel so comfortable and didn't rush us or make us feel like the odd ones out! The other people in the tour were also incredibly friendly. I would recommend this tour to everyone and anyone heading to or living in Chicago. So worth the money! Definitley going back for more! Can't wait for the HOLIDAY TOUR! Thanks much Dan!

lois2468 .

October 8, 2013

We thoroughly enjoyed our River Walk Tour with Dan O'Donnell as our guide. We've lived in Chicago forever and learned so many things we never knew. Dan was so knowledgeable and had answers for all our questions. It was nice that the tour was split in 2 parts with a delicious brunch in the middle. We would definitely recommend this tour to everyone. I walk with a cane and had no problems keeping up with the group.

Julio C.

October 5, 2013

Me and my girlfriend and her son did on Saturday the River walk Chicago History Tour with Rick as our tour guide and I definitely give this tour a 5 star award and not just any 5 star award the Richlatino 5 star award. Was very fun and its always great to know where you came from if you were born and raised in Chicago IL like me. Was an awesome tour and my Fedora hat is off to this tour company. If you haven't done this before then you really should. I can guarantee you will love it. And many know when I post a great review I mean every word. The Latino in the Fedora Hat never lies. So definitely I recommend doing this tour. Just go and experience it. I loved it and Rick was an awesome tour guide!

Lou A.

October 5, 2013

The River Walk tour was great! Our host was Dan O’Connell and he was very personable with a good sense of humor which made the tour fun for all. The event was just as described – an enjoyable and leisurely walk along the river with a delicious brunch half way through. We learned a lot of information and saw our beautiful city from a new perspective. I would recommend this tour for visitors as well as fellow Chicagoans.

5Kathy416 .

October 1, 2013

My parents and I spent the morning on Chicago's Finest River Walk Tour. It was a delightful and educational experience. Our guide Daniel O'Connell was very knowledgeable. He was informative and kept everyone’s attention with a diverse amount of trivia and information. We highly recommend the outing to others. It was a lovely way to spend the morning.

Ana R.

September 30, 2013

This was a great excursion I'm born and grew up in the city and I learned so much our tour guide was so knowledgable kept the whole group engaged with his trivia questions and jokes. I went with a group of co-workers who ranged from mid 30's to almost retirement age and all of us enjoyed and loved the expierence. I've just been talking about it all weekend long to family and friends telling them they should plan to take this tour. I think you'll be seeing us again next fall.

Thanks Ana R.

Jennifer W.

September 27, 2013

The Roaring 20s River Walk Tour is a fantastic tour with a minimal amount of walking. There were also places for us to sit and relax along the way. Dan, our tour guide, gave us folders containing an itinerary, photos, facts, etc. regarding the topics covered from this era. He also engaged us in a fun trivia challenge along the way. Dan was considerate of his "guests" and made sure that everyone was gathered around him and that we all could hear him and the sun was in HIS eyes, not ours-his enthusiasm was contagious! The tour lasted 2 1/2 hrs and my friend and I both thought that the experience was awesome! Trying another tour next month!

CathyK1955 .

August 22, 2013

If you're in Chicago for the day, make sure you check out Chicago's Finest River Walk Tour. It's a great way to discover all the hidden gems the city has to offer. Our tour guide Dan, was fantastic! He is very knowledgeable about the city and kept everyone entertained with Chicago trivia.

nm4travel .

July 31, 2013

This review is for the Finest of Everything tour which is Chicago's Finest newest tour. It was fun. We were in town for a few days, and it was great to walk through the Chicago pedway, (I would have never known it existed), some of the old buildings and learn about the architecture and learn the layout of the city. We also took the water taxi and that was a great little extra!

Patty M.

July 30, 2013

Had a great tour in Chicago last week. Took the Roaring 20's tour with Dan and Sharon as our guides. They shared so much information in an interesting and fun way. We met some lovely people in our group and had a great time. Next time in Chicago, I will definitely do another walk with them.

Janet S.

June 28, 2013

Even though I have lived in Chicago all of my life I have never taken advantage of some of the things that are offered in the Loop. So, I decided it was about time to do something about it.

While browsing the internet I came across Chicago's Finest Tours. It sounded interesting so I booked it. I met Dan and Sharon a little before our tour was to start. Our group then went to the River Walk. I could have listened to Dan's and Sharon's story telling all evening. The group split into groups for Dan's Trivia questions. Getting the questions right and first gave your team points for great prizes. I thought I new Chicago but I think I came in last. Another surprise was a drink and appetizer at O'Brian's while he continued telling us about how Chicago grew and the characters of that Roaring time.

I would recommend this tour to anyone young and old. I would like to take their Pedway tour in the fall.

hoosierkathy .

June 16, 2013

Not knowing what to expect....I was wowed by this tour. Dan's enthusiasm and sharing his long-time love for the history of Chicago made it so exciting and interesting. His little games of True and False kept everyone on their toes hoping for a wonderful prize! I'm hungry for more information on this wonderful city. We were fed great food at our brunch and Dan kept on feeding our minds during this also. So much was shared with our group you couldn't possible retain it all. I'll have to go back for another Chicago River Walk Tour....soon! Thank you so much Dan.

Jody A.

June 8, 2013

Thoroughly enjoyed every minute of this tour. Dan was the best tour guide I could have asked for - he was an endless source of great stories making history FUN. I was blown away by how much I learned about Chicago in a few hours! Time flew by!

Great gift from my son and his girlfriend!

RetiredTeacher09 .

June 4, 2013

The Historic Pedway Tour was completing its winter schedule when we joined a group of 20 with our group of 6. Rick was a prolific source of history from the very beginnings of Chicago to the present time. The map of the pedway system was fascinating. You can walk for several blocks both south and east of the river. Stopoffs along the way include a fascinating look at the architectural beauty of the Cultural Center (formerly the Chicago Library) and the Thompson Center is another view. There are questions along the way both from the facilitator and the group. Treats were dispensed after teasingly taking the group through Macy's candy emporium. The ending of the tour completed with an above ground pedway ending at the Renaissance Hotel. Thoroughly enjoyed the 2 1/2 hours that went very fast. There are stairs but not a strenuous walk.

deb69_14 .

June 1, 2013

Dan led a larger-than-usual group (27) on a fascinating tour of the Chicago Pedway, entertaining and educating us with Chicago historical, architectural, and cultural facts all the way. Despite the unusually large group, Dan was able to answer all questions and provide a good time for everyone.While I'd been in parts of the Pedway before, now i can avoid the wind, rain, snow, and cold throughout most of the Loop. Dan made sure we could hear and understand him; that we had bathroom breaks as needed; and that if we had questions, they were answered. I can't wait to do the River Walk.

Linda B.

May 31, 2013

Fantastic! Our guide Rick was wonderful, knowledgeable, patient and witty. I have lived in the area all my life, and even worked downtown Chicago for 18 years and still learned so much. Every Chicagoan should know the facts about our city.

My husband and I have also taken the Chicago's Finest River Walk Tour and really loved it.

Can't wait to try another.

Dianna C.

May 4, 2013

Chicago History Lovers Pedway Tour on a Sunday afternoon. Our guide, was amazing. I not sure how he remembered what he didn't They, provided us wtih notebooks that we could carry on the tour that contained all kinds of information and visual aids to help us follow along. I don't know how he remembers all of that detail. But, I can guarantee you this: You will most certainly learn something new during this tour. It was nice if you go on a rainy -cold day you are mainly indoors so no worry about the weather ruining your time.

Katie K.

April 28, 2013

My fiance and I love to try new things in the city-and this is a must. The Chicago History/Pedway tour was fantastic. We loved the tour, fun facts, trivia game, and especially the tour guide Dan. He is such an enthusiastic tour guide and full of knowledge. Whenever we do another Chicago tour, we will make sure to check out your website first! Thank you!

happywindsor .

March 31, 2013

Daniel gave us an incredibly in-depth historical overview of Chicago's beginning and right up to present. I had never been down into the pedways before. We were given a map to keep which I really appreciated. Daniel's recount was lively and interactive. It was well worth the ticket and a great value for the price. I would highly recommend this for anyone wanting to do more in Chicago than shop.

StephanieM72 .

February 17, 2013

I moved to Chicago a year ago and my mom was in town so we decided to try out the Pedway tour. I"m not a "history buff" or anything like that but this was a really neat way to see the city - I'd never even heard of the pedway before this. We did the History tour and Dan O'Connell was an amazing guide. He's obviously passionate about this city and its history and was able to teach us more while we all had a good time. I definitely recommend it to anyone who wants to learn more about the city you walk through every day or the city you're just visiting for the first time!

Kim A.

January 21, 2013

Rick was our guide. We learned fantastic details about Chicago that we never knew and saw things we never would have seen without the tour. We even checked Rick's facts after the tour and he was dead on. Rick is a GREAT story teller, he kept our attention and added great humor. Wonderful value!

DebLF .

December 30, 2012

My family and I recently took the pedway history tour and we are from the Chicago land area. We found this tour to be full of interesting facts and new info about Chicago. Guide was great - nice mix of history and wit.

M G.

December 2, 2012

If you're looking for an abundance of facts and history on Chicago this is the tour for you. If, however, you're interested in learning more about the history or navigation of the Pedway system, or some of the buildings you can access through it, try another tour company. This particular "walking tour" was really more of a standing tour - and ALOT of it. The walking aspect is just so the group can move from one gathering place to the next. Our guide Don was full of information but wasn't inclined to answer questions outside of his script. I realize this was a "history" tour and not an architectural tour but how can you take visitors into a gorgeous building like the Cultural Center and offer so little info on it? The building seemed like an afterthought - somewhere to conduct the history lecture while keeping people out of the winter weather. The same could be said for the Pedway system. We used it to get from point A to point B but there was no description of it's history, how it connects, etc. The tour ended up running 3.5 hrs but if the chorus of yawns was any indication, most of the group gave up interest 2 hrs prior.

Erica H.

September 20, 2012

I'm a Chicago native and I took an out-of-town visitor on the River Walk Tour. We had a great time! What I loved about the tour guide (Dan) is that he told stories, which are so much easier for me to digest, appreciate, and remember than straight facts. We mostly stayed around the intersection of the river with Michigan Avenue and he crafted a 2 and a half hour presentation covering everything from DuSable and the Ft. Dearborn Massacre to the Chicago Fire and Walt Disney. Really, it was wonderful and NOT cheesy, which so many tours can be. I would definitely go on another one of their tours, with out-of-town visitors or not!

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